Diisopropylethylamine → (1R,4R,5R)-N-[(1S)-1-[[[(1S)-1-Cyclohexyl-2-(methylamino)-2-oxoethyl]amino]carbonyl]-2,2-dimethylpropyl]-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	3-Oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid	HCID 46244965	—
Reactant	HCID 68491417	HCID 68491417	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(1R,4R,5R)-N-[(1S)-1-[[[(1S)-1-Cyclohexyl-2-(methylamino)-2-oxoethyl]amino]carbonyl]-2,2-dimethylpropyl]-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxamide	HCID 68490886	93.2%

Reaction Conditions

Temperature	0 °C

Reaction Steps

To a solution of compound 32 (53 mg, 0.34 mmol) in DMF (9 mL) was added compound 65 (80 mg, 0.28 mmol) and DIEA (290 □L, 1.66 mmol). The solution was cooled to 0° C. and HATU (127 mg, 0.33 mmol) was added. After stirring at 0° C. for 1 h and at rt for 1 h the solvent was evaporated, and the crude product was purified by flash column chromatography (EtOAc/toluene 2:1) to give compound 72 (110 mg, 92%) as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07671032B2
Source dataset	uspto-grants-2010_03
ORD ID	ord-5ac40fb678a74f0492cbddac3de57f0a
Source note	uspto-grants-2010_03